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1.
Chem Biodivers ; 21(8): e202400944, 2024 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-38828873

RESUMEN

The study of new plant species and the identification of their chemical composition may contribute to the discovery of a new breakthrough substances for pharmacotherapeutical applications. For the first time, we examined antioxidant and antimicrobial activity of 70 % v/v methanolic extracts from inflorescences and roots of Cirsium monspessulanum (L.) Hill. obtained by the ASE method. In the (2,2-diphenyl-1-picrylhydrazyl) DPPH analysis, tested extract of inflorescences showed antioxidant activity with an EC50=0.223±0.0479 mg/mL, and (Cupric Ion Reducting Antioxidant Capacity) CUPRAC test assessed the antiradical activity on 14.95±0.13 mgTE/g and for roots the values were EC50=0.307±0.0554 mg/mL and 11.18±0.49 mgTE/g, respectively. Furthermore, extract from the inflorescences possessed the highest antimicrobial activity against Staphylococcus aureus, Staphylococcus epidermidis and Micrococcus luteus with MIC=1.25 mg/mL for each. HPLC/ESI-QTOF-MS/MS method identified 7 phenolic acids and 14 flavonoids in inflorescences extract and only 7 phenolic acids in roots extract. To the best of our knowledge, this is the first qualitative analysis of Cirsium monspessulanum (L.) Hill. and all substances were described for the first time.


Asunto(s)
Antibacterianos , Antioxidantes , Cirsium , Metanol , Pruebas de Sensibilidad Microbiana , Fitoquímicos , Extractos Vegetales , Staphylococcus aureus , Cirsium/química , Extractos Vegetales/farmacología , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Antioxidantes/farmacología , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Fitoquímicos/farmacología , Fitoquímicos/química , Fitoquímicos/aislamiento & purificación , Staphylococcus aureus/efectos de los fármacos , Metanol/química , Micrococcus luteus/efectos de los fármacos , Staphylococcus epidermidis/efectos de los fármacos , Compuestos de Bifenilo/antagonistas & inhibidores , Raíces de Plantas/química , Picratos/antagonistas & inhibidores
2.
Sensors (Basel) ; 24(5)2024 Feb 27.
Artículo en Inglés | MEDLINE | ID: mdl-38475060

RESUMEN

Rhodanine-3-acetic acid derivatives are attractive compounds with versatile effects. What is very important is that compounds of this type have many biological properties. They are tested, among others, as fluorescent probes for bioimaging and aldose reductase inhibitors. Rhodanine-3-acetic acid derivatives also have antibacterial, antifungal and anticancer activity. The presented work demonstrates that a slight change in the five-membered heterocyclic substituent significantly affects the properties of the compounds under consideration. Three rhodanine-3-acetic acid derivatives (A-1-A-3) were obtained in the Knoevenagel condensation reaction with good yields, ranging from 54% to 71%. High thermal stability of the tested compounds was also demonstrated above 240 °C. The absorption and emission maxima in polar and non-polar solvents were determined. Then, the possibility of using the considered derivatives for fluorescence bioimaging was checked. Compounds A-1 and A-2 were successfully used as fluorescent dyes of fixed cells of mammalian origin. In addition, biological activity tests against bacteria and fungi were carried out. Our results showed that A-1 and A-2 showed the most excellent antimicrobial activity among the newly synthesized compounds, especially against Gram-positive bacteria.


Asunto(s)
Ácido Acético , Rodanina , Animales , Ácido Acético/química , Rodanina/química , Rodanina/farmacología , Antibacterianos/farmacología , Inhibidores Enzimáticos , Hongos , Pruebas de Sensibilidad Microbiana , Mamíferos
3.
Molecules ; 29(19)2024 Oct 04.
Artículo en Inglés | MEDLINE | ID: mdl-39407631

RESUMEN

The search for safe, cheap, and repeatable diagnostic methods is a fundamental research goal. Currently, great hope is placed on fluorescence imaging. However, the development of this method mainly depends on efficient fluorescent probes. Designing and obtaining new probes with potential applications in fluorescence imaging is very difficult because compounds of this type must meet several requirements related to their properties. Therefore, this article attempted to obtain and study new phenanthro[9,10-d]-imidazole derivatives (PK1-PK3) with potential application as fluorescent probes for fluorescence imaging. The main goal of the work was to assess the effect of two functional groups (such as the formyl group (PK2) and rhodanine-3-acetic acid (PK3)) on selected physicochemical properties and possibilities of practical application of the considered compounds. The conducted studies proved that the influence of the functional group is significant, as it causes a bathochromic shift in both absorption and emission results (by the order PK1 < PK2 < PK3). Moreover, all compounds could stain live cells cultured in vitro. The staining efficiency was not affected by the cell line, thanks to which we obtained the correct staining of both mouse and human cell lines. PK3 was the most attractive of the tested compounds due to its staining potential of live cells and retention after fixation. Our results also showed some antibacterial and antifungal activity of the newly synthesized compounds (PK1-PK3). Among them, PK3 showed the highest antimicrobial effect, especially against Gram-positive bacteria.


Asunto(s)
Imidazoles , Imidazoles/química , Imidazoles/farmacología , Imidazoles/síntesis química , Humanos , Ratones , Animales , Colorantes Fluorescentes/química , Pruebas de Sensibilidad Microbiana , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/síntesis química , Imagen Óptica/métodos , Estructura Molecular
4.
Molecules ; 29(16)2024 Aug 11.
Artículo en Inglés | MEDLINE | ID: mdl-39202893

RESUMEN

Nowadays, searching for novel antimicrobial agents is crucial due to the increasing number of resistant bacterial strains. Moreover, cancer therapy is a major challenge for modern medicine. Currently used cytostatics have a large number of side effects and insufficient therapeutic effects. Due to the above-mentioned facts, we undertook research to synthesize novel compounds from the acylhydrazone group aimed at obtaining potential antimicrobial and anticancer agents. As a starting material, we employed hydrazides of 2-, 3- or 4-iodobenzoic acid, which gave three series of acylhydrazones in the condensation reaction with various aldehydes. The chemical structure of all obtained compounds was confirmed by IR, 1H NMR, and 13C NMR. The structure of selected compounds was determined by single-crystal X-ray diffraction analysis. Additionally, all samples were characterized using powder X-ray diffraction. The other issue in this research was to examine the possibility of the solvent-free synthesis of compounds using mechanochemical methods. The biological screening results revealed that some of the newly synthesized compounds indicated a beneficial antimicrobial effect even against MRSA-the methicillin-resistant Staphylococcus aureus ATCC 43300 strain. In many cases, the antibacterial activity of synthesized acylhydrazones was equal to or better than that of commercially available antibacterial agents that were used as reference substances in this research. Significantly, the tested compounds do not show toxicity to normal cell lines either.


Asunto(s)
Antibacterianos , Hidrazonas , Pruebas de Sensibilidad Microbiana , Hidrazonas/química , Hidrazonas/farmacología , Hidrazonas/síntesis química , Humanos , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/síntesis química , Yodobenzoatos/química , Antineoplásicos/farmacología , Antineoplásicos/química , Antineoplásicos/síntesis química , Estructura Molecular , Staphylococcus aureus Resistente a Meticilina/efectos de los fármacos , Cristalografía por Rayos X , Relación Estructura-Actividad , Antiinfecciosos/farmacología , Antiinfecciosos/química , Antiinfecciosos/síntesis química
5.
Int J Mol Sci ; 24(21)2023 Nov 01.
Artículo en Inglés | MEDLINE | ID: mdl-37958861

RESUMEN

The effects of physical factors such as radiation (electromagnetic, microwave, infrared, laser, UVC, and X-ray) and high temperature, as well as chemical factors (controlled atmosphere) on the level of global DNA cytosine methylation in C. albicans ATCC 10231 cells were investigated. Prolonged exposure to each type of radiation significantly increased the DNA methylation level. In addition, the global methylation level in C. albicans cells increased with the incubation temperature. An increase in the percentage of methylated DNA was also noted in C. albicans cells cultured in an atmosphere with reduced O2. In contrast, in an atmosphere containing more than 3% CO2 and in anaerobic conditions, the DNA methylation level decreased relative to the control. This study showed that prolonged exposure to various types of radiation and high temperature as well as reduced O2 in the atmosphere caused a significant increase in the global DNA methylation level. This is most likely a response protecting DNA against damage, which at the same time can lead to epigenetic disorders, and in consequence can adversely affect the functioning of the organism.


Asunto(s)
Candida albicans , Metilación de ADN , Candida albicans/genética , Daño del ADN , ADN , Atmósfera , Epigénesis Genética
6.
Int J Mol Sci ; 24(24)2023 Dec 14.
Artículo en Inglés | MEDLINE | ID: mdl-38139308

RESUMEN

In this research, twenty-four hydrazide-hydrazones of 2,4-dihydroxybenzoic acid were designed, synthesized, and subjected to in vitro and in vivo bioactivity studies. The chemical structure of the obtained compounds was confirmed by spectral methods. Antimicrobial activity screening was performed against a panel of microorganisms for all synthesized hydrazide-hydrazones. The performed assays revealed the interesting antibacterial activity of a few substances against Gram-positive bacterial strains including MRSA-Staphylococcus aureus ATCC 43300 (compound 18: 2,4-dihydroxy-N-[(2-hydroxy-3,5-diiodophenyl)methylidene]benzohydrazide-Minimal Inhibitory Concentration, MIC = 3.91 µg/mL). In addition, we performed the in vitro screening of antiproliferative activity and also assessed the acute toxicity of six hydrazide-hydrazones. The following human cancer cell lines were used: 769-P, HepG2, H1563, and LN-229, and the viability of the cells was assessed using the MTT method. The HEK-293 cell line was used as a reference line. The toxicity was tested in vivo on Danio rerio embryos using the Fish Embryo Acute Toxicity (FET) test procedure according to OECD No. 236. The inhibitory concentration values obtained in the in vitro test showed that N-[(4-nitrophenyl)methylidene]-2,4-dihydroxybenzhydrazide (21) inhibited cancer cell proliferation the most, with an extremely low IC50 (Inhibitory Concentration) value, estimated at 0.77 µM for LN-229. In addition, each of the compounds tested was selective against cancer cell lines. The compounds with a nitrophenyl substituent were the most promising in terms of inhibition cancer cell proliferation. The toxicity against zebrafish embryos and larvae was also very low or moderate.


Asunto(s)
Antineoplásicos , Hidrazonas , Animales , Humanos , Hidrazonas/farmacología , Hidrazinas/farmacología , Hidrazinas/química , Células HEK293 , Pez Cebra , Relación Estructura-Actividad , Pruebas de Sensibilidad Microbiana , Antineoplásicos/química
7.
Int J Mol Sci ; 23(5)2022 Mar 04.
Artículo en Inglés | MEDLINE | ID: mdl-35269966

RESUMEN

In our research, we used nicotinic acid as a starting compound, which was subjected to a series of condensation reactions with appropriate aldehydes. As a result of these reactions, we were able to obtain a series of twelve acylhydrazones, two of which showed promising activity against Gram-positive bacteria (MIC = 1.95-15.62 µg/mL), especially against Staphylococcus epidermidis ATCC 12228 (MIC = 1.95 µg/mL). Moreover, the activity of compound 13 against the Staphylococcus aureus ATCC 43300 strain, i.e., the MRSA strain, was MIC = 7.81 µg/mL. Then, we subjected the entire series of acylhydrazones to a cyclization reaction in the acetic anhydride, thanks to which we were able to obtain twelve new 3-acetyl-2,5-disubstituted-1,3,4-oxadiazoline derivatives. Obtained 1,3,4-oxadiazolines were also tested for antimicrobial activity. The results showed high activity of compound 25 with a 5-nitrofuran substituent, which was active against all tested strains. The most promising activity of this compound was found against Gram-positive bacteria, in particular against Bacillus subtilis ATCC 6633 and Staphylococcus aureus ATCC 6538 (MIC = 7.81 µg/mL) and ATCC 43300 MRSA strains (MIC = 15.62 µg/mL). Importantly, the best performing compounds did not show cytotoxicity against normal cell lines. It seems practical to use some of these compounds or their derivatives in the future in the prevention and treatment of infections caused by some pathogenic or opportunistic microorganisms.


Asunto(s)
Niacina , Antibacterianos/farmacología , Bacillus subtilis , Pruebas de Sensibilidad Microbiana , Simulación del Acoplamiento Molecular , Staphylococcus aureus , Relación Estructura-Actividad
8.
Molecules ; 28(1)2022 Dec 26.
Artículo en Inglés | MEDLINE | ID: mdl-36615409

RESUMEN

The occurrence of candidiasis, including superficial infections, has recently increased dramatically, especially in immunocompromised patients. Their treatment is often ineffective due to the resistance of yeasts to antimycotics. Therefore, there is a need to search for new antifungals. The aim of this study was to determine the antifungal effect of clove essential oil (CEO) and eugenol (EUG) towards both reference and clinical Candida spp. strains isolated from the oral cavity of patients with hematological malignancies, and to investigate their mode of action and the interactions in combination with the selected antimycotics. These studies were performed using the broth microdilution method, tests with sorbitol and ergosterol, and a checkerboard technique, respectively. The CEO and EUG showed activity against all Candida strains with a minimal inhibitory concentration (MIC) in the range of 0.25-2 mg/mL. It was also found that both natural products bind to ergosterol in the yeast cell membrane. Moreover, the interactions between CEO and EUG with several antimycotics-cetylpyridinium chloride, chlorhexidine, silver nitrate and triclosan-showed synergistic or additive effects in combination, except nystatin. This study confirms that the studied compounds appear to be a very promising group of phytopharmaceuticals used topically in the treatment of superficial candidiasis. However, this requires further studies in vivo.


Asunto(s)
Candidiasis , Aceites Volátiles , Syzygium , Humanos , Antifúngicos , Candida , Eugenol/farmacología , Eugenol/uso terapéutico , Candidiasis/tratamiento farmacológico , Aceite de Clavo/farmacología , Aceite de Clavo/uso terapéutico , Ergosterol/farmacología , Pruebas de Sensibilidad Microbiana
9.
Molecules ; 27(24)2022 Dec 16.
Artículo en Inglés | MEDLINE | ID: mdl-36558125

RESUMEN

Ziziphora species (Lamiaceae) have been used in traditional medicine as sedatives, antiseptics, carminatives, or expectorants. Despite their common applications in phytotherapy, there is still lack of evidence about the composition of their extracts and its impact on biological properties of the plants. The aim of this study was to evaluate the content of Ziziphora bungeana, a less studied species growing in Kazakhstan, using HPLC-ESI-QTOF-MS/MS instrumentation and to determine its antimicrobial, antioxidant, and cytotoxic activity together with inhibitory properties against tyrosinase and toxicity in erythrocyte lysis assay. Extracts from Z. bungeana were found to be sources of flavonoids, phenolic acids, organic acids, and terpenes that determined their antiradical activity. The minimum inhibitory concentrations of extracts were lower for Gram-positive bacteria (1.25-10 mg/mL) than for Gram-negative bacteria and fungi (5-20 mg/mL). The EC50 value calculated for antiradical activity ranged between 15.00 ± 1.06 µg/mL and 13.21 ± 3.24 µg/mL for ABTS and DPPH assays, respectively. Z. bungeana extracts were found to decrease the activity of tyrosinase by 50% (at 200 µg/mL) similarly to kojic acid and were slightly cytotoxic for human melanoma A375 cell line (at 200 µg/mL) with no effect on HaCaT keratinocytes. In the end, Z. bungeana did not reveal toxic effects in hemolytic assay as compared to the positive control Triton X-100. The performed tests show potential application of the plant in the treatment of infectious diseases, disorders caused by free radicals, and skin problems.


Asunto(s)
Lamiaceae , Extractos Vegetales , Humanos , Extractos Vegetales/farmacología , Extractos Vegetales/química , Monofenol Monooxigenasa , Espectrometría de Masas en Tándem , Fitoquímicos/farmacología , Lamiaceae/química , Antioxidantes/farmacología , Antioxidantes/química , Flavonoides/farmacología
10.
Appl Microbiol Biotechnol ; 105(16-17): 6355-6367, 2021 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-34410437

RESUMEN

Recently, the occurrence of candidiasis has increased dramatically, especially in immunocompromised patients. Additionally, their treatment is often ineffective due to the resistance of yeasts to antimycotics. Therefore, there is a need to search for new antifungals. A series of nine newly synthesized thiazole derivatives containing the cyclopropane system, showing promising activity against Candida spp., has been further investigated. We decided to verify their antifungal activity towards clinical Candida albicans isolated from the oral cavity of patients with hematological malignancies and investigate the mode of action on fungal cell, the effect of combination with the selected antimycotics, toxicity to erythrocytes, and lipophilicity. These studies were performed by the broth microdilution method, test with sorbitol and ergosterol, checkerboard technique, erythrocyte lysis assay, and reversed phase thin-layer chromatography, respectively. All derivatives showed very strong activity (similar and even higher than nystatin) against all C. albicans isolates with minimal inhibitory concentration (MIC) = 0.008-7.81 µg/mL Their mechanism of action may be related to action within the fungal cell wall structure and/or within the cell membrane. The interactions between the derivatives and the selected antimycotics (nystatin, chlorhexidine, and thymol) showed additive effect only in the case of combination some of them and thymol. The erythrocyte lysis assay confirmed the low cytotoxicity of these compounds as compared to nystatin. The high lipophilicity of the derivatives was related with their high antifungal activity. The present studies confirm that the studied thiazole derivatives containing the cyclopropane system appear to be a very promising group of compounds in treatment of infections caused by C. albicans. However, this requires further studies in vivo. KEY POINTS: • The newly thiazoles showed high antifungal activity and some of them - additive effect in combination with thymol. • Their mode of action may be related with the influence on the structure of the fungal cell wall and/or the cell membrane. • The low cytotoxicity against erythrocytes and high lipophilicity of these derivatives are their additional good properties.


Asunto(s)
Antifúngicos , Candida albicans , Antifúngicos/farmacología , Antifúngicos/uso terapéutico , Candida , Humanos , Pruebas de Sensibilidad Microbiana , Nistatina , Tiazoles
11.
Int J Mol Sci ; 22(24)2021 Dec 20.
Artículo en Inglés | MEDLINE | ID: mdl-34948461

RESUMEN

Antibiotic resistance is now a global problem, and the lack of effective antimicrobial agents for the treatment of diseases caused by resistant microbes is increasing. The 3-acetyl-2,5-disubstituted-1,3,4-oxadiazolines presented in this article may provide a good starting point for the development of potential new effective antimicrobial agents useful in the treatment of bacterial and fungal infections. Particular attention is drawn to the 1,3,4-oxadiazole derivative marked with the number 29 with 5-nitrofuran-2-yl substituent in its chemical structure. This substance showed a strong bactericidal effect, especially against Staphylococcus spp., and no cytotoxicity to the L929 normal cell line.


Asunto(s)
Antibacterianos/farmacología , Farmacorresistencia Bacteriana , Oxadiazoles/farmacología , Staphylococcus/crecimiento & desarrollo , Antibacterianos/síntesis química , Antibacterianos/química , Línea Celular , Humanos , Pruebas de Sensibilidad Microbiana , Viabilidad Microbiana/efectos de los fármacos , Estructura Molecular , Oxadiazoles/síntesis química , Oxadiazoles/química , Staphylococcus/efectos de los fármacos , Relación Estructura-Actividad
12.
Molecules ; 26(24)2021 Dec 13.
Artículo en Inglés | MEDLINE | ID: mdl-34946632

RESUMEN

Many of the essential oils obtained from medicinal plants possess proven antimicrobial activity and are suitable for medicinal purposes and applications in the food industry. The aim of the present work was the chemical analysis of 19 essential oils (EOs) from seven different Cymbopogon species (C. nardus, C. citratus, C winterianus, C. flexuosus, C. schoenanthus, C. martinii, C. giganteus). Five different chemotypes were established by GC/MS and TLC assay. The EOs, as well as some reference compounds, i.e., citronellol, geraniol and citral (neral + geranial), were also tested for their antimicrobial and antibiofilm activity against methicillin-resistant Staphylococcus aureus (MRSA) by the microdilution method and direct bioautography. The toxicity of EOs was evaluated by Danio rerio 'Zebrafish' model assay. All examined EOs showed moderate to high activity against MRSA, with the highest activity noted for C. flexuosus-lemongrass essential oil, both in microdilution and direct autobiography method. Significant difference in the toxicity of the examined EOs was also detected.


Asunto(s)
Antibacterianos , Biopelículas/efectos de los fármacos , Cymbopogon/química , Staphylococcus aureus Resistente a Meticilina/fisiología , Aceites Volátiles , Antibacterianos/química , Antibacterianos/farmacología , Biopelículas/crecimiento & desarrollo , Aceites Volátiles/química , Aceites Volátiles/farmacología , Especificidad de la Especie
13.
Molecules ; 25(24)2020 Dec 10.
Artículo en Inglés | MEDLINE | ID: mdl-33322054

RESUMEN

The aim of our study was the two-stage synthesis of 1,3,4-oxadiazole derivatives. The first step was the synthesis of hydrazide-hydrazones from 3-methyl-4-nitrobenzhydrazide and the corresponding substituted aromatic aldehydes. Then, the synthesized hydrazide-hydrazones were cyclized with acetic anhydride to obtain new 3-acetyl-2,3-disubstituted-1,3,4-oxadiazolines. All of obtained compounds were tested in in vitro assays to establish their potential antimicrobial activity and cytotoxicity. Our results indicated that few of the newly synthesized compounds had some antimicrobial activity, mainly compounds 20 and 37 towards all used reference bacterial strains (except Klebsiella pneumoniae, Proteus mirabilis, and Pseudomonas aeruginosa) and fungi. These substances showed a strong or powerful bactericidal effect, especially against Staphylococcus spp. belonging to Gram-positive bacteria. Compound 37 was active against Staphylococcus epidermidis at minimal inhibitory concentration (MIC) = 0.48 µg/mL and was characterized by low cytotoxicity. This compound possessed quinolin-4-yl substituent in the second position of 1,3,4-oxadiazole ring and 3-methyl-4-nitrophenyl in position 5. High effectiveness and safety of these derivatives make them promising candidates as antimicrobial agents. Whereas the compound 20 with the 5-iodofurane substituent in position 2 of the 1,3,4-oxadiazole ring showed the greatest activity against S. epidermidis at MIC = 1.95 µg/mL.


Asunto(s)
Antiinfecciosos/síntesis química , Antiinfecciosos/farmacología , Oxadiazoles/síntesis química , Oxadiazoles/farmacología , Animales , Antibacterianos/síntesis química , Antibacterianos/química , Antibacterianos/farmacología , Antiinfecciosos/química , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Técnicas de Química Sintética , Relación Dosis-Respuesta a Droga , Humanos , Ratones , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Oxadiazoles/química , Relación Estructura-Actividad
14.
Chem Biodivers ; 16(6): e1900082, 2019 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-31050208

RESUMEN

Thirteen new 3-acetyl-2,5-disubstituted-1,3,4-oxadiazoline derivatives were synthesized from corresponding hydrazide-hydrazones of isonicotinic acid in the reaction with acetic anhydride. The obtained compounds were identified with the use of spectral methods (IR, 1 H-NMR, 13 C-NMR, MS). In vitro antimicrobial activity screening of synthesized compounds against a panel of bacteria and fungi revealed interesting antibacterial and antifungal activity of tested 1,3,4-oxadiazoline derivatives, which is comparable to that of commonly used antimicrobial agents.


Asunto(s)
Antiinfecciosos/síntesis química , Oxadiazoles/química , Antiinfecciosos/química , Antiinfecciosos/farmacología , Hongos/efectos de los fármacos , Bacterias Gramnegativas/efectos de los fármacos , Bacterias Grampositivas/efectos de los fármacos , Pruebas de Sensibilidad Microbiana , Oxadiazoles/síntesis química , Oxadiazoles/farmacología
15.
Saudi Pharm J ; 27(4): 593-601, 2019 May.
Artículo en Inglés | MEDLINE | ID: mdl-31061629

RESUMEN

The process of searching for new antibacterial agents is more and more challenging due to the increasing drug resistance which has become a major concern in the field of infection management. Our study presents a synthesis and characterization by IR, UV, 1H NMR and 13C NMR spectra of a homogenous series of 1-EWG functionalized 2-aryl-1-nitroethenes which could prove good candidates for the replacement of traditional antibacterial drugs In vitro screening against a panel of the reference strains of bacteria and fungi and their cytotoxicity towards cultured human HepG2 and HaCaT cells was performed. Antimicrobial results indicated that four of the synthesized compounds exhibited a significant antimicrobial activity against all tested reference bacteria and fungi belonging to yeasts with a specific and strong activity towards B. subtilis ATCC 6633. Two of these compounds had no detectable cytotoxicity towards the cultured human cell lines, making them promising candidates for new antibacterial drugs.

16.
Med Chem Res ; 27(9): 2125-2140, 2018.
Artículo en Inglés | MEDLINE | ID: mdl-30220831

RESUMEN

Synthesis and investigation of antifungal, anticonvulsant and anti-Toxoplasma gondii activities of ten novel (2-(cyclopropylmethylidene)hydrazinyl)thiazole 3a-3j are presented. Among the derivatives, compounds 3a-3d and 3f-3j possess very high activity against Candida spp. ATCC with MIC = 0.015-7.81 µg/ml. Compounds 3a-3d and 3f-3j possess also very high activity towards most of strains of Candida spp. isolated from clinical materials with MIC = 0.015-7.81 µg/ml. The activity of these compounds is similar and even higher than the activity of nystatin used as positive control. Additionally, compounds 3c and 3e showed interesting anticonvulsant activities in the MES test, whereas compounds 3f and 3i demonstrated the anticonvulsant activity in PTZ-induced seizures. Noteworthy, none of these compounds impaired animals' motor skills in the rotarod test. Moreover, thiazoles 3a, 3h, and 3j showed significant anti-Toxoplasma gondii activity, with IC50 values 31-52 times lower than those observed for sulfadiazine. The results of the cytotoxicity evaluation, anti-Candida spp. and anti-Toxoplasma gondii activity studies showed that Candida spp. and Toxoplasma gondii growth was inhibited at non-cytotoxic concentrations for the mouse L929 fibroblast and the African green monkey kidney (VERO) cells. Molecular docking studies indicated secreted aspartic proteinase (SAP) as possible antifungal target.

17.
Chem Biodivers ; 14(8)2017 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-28444991

RESUMEN

The main aim of this research was the synthesis, spectral identification and in vitro antimicrobial evaluation of new hydrazides and hydrazide-hydrazones of 2,3-dihalogen substituted propionic acids. New hydrazides were obtained by the substitution reaction of appropriate ethyl esters of 2,3-dihalogen substituted propionic acids with hydrazine hydrate. Then obtained hydrazides were subjected to condensation reaction with various aldehydes which yielded with new hydrazide-hydrazone derivatives. All obtained compounds were identified on the basis of spectral methods (1 H-NMR, 13 C-NMR) and in vitro screened against a panel of bacterial and fungal strains according to EUCAST and CLSI guidelines.


Asunto(s)
Antiinfecciosos/química , Hidrazinas/química , Hidrazonas/química , Propionatos/química , Antiinfecciosos/síntesis química , Antiinfecciosos/farmacología , Hongos/efectos de los fármacos , Bacterias Gramnegativas/efectos de los fármacos , Bacterias Grampositivas/efectos de los fármacos , Hidrazinas/síntesis química , Hidrazinas/farmacología , Hidrazonas/síntesis química , Hidrazonas/farmacología , Pruebas de Sensibilidad Microbiana
18.
Acta Pol Pharm ; 74(1): 161-172, 2017 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-29474772

RESUMEN

In this work the phenolic acids in crude methanol extracts from the flowering herbs of Carluus acanthoides L. were identified. The samples containing free phenolic acids and those released after acid and alka- line hydrolyses were investigated by 2D TLC on cellulose. After purification by SPE, samples were also analyzed by RP-HPLC. Chlorogenic, protocatechuic, p- coumaric, caffeic, syringic, p-hydroxybenzoic, ferulic, vanillic, gentisic and gallic acids were detected in fractions of the methanolic extract obtained from the flow- ering herb of C. acanthoides. This is the first study concerning the qualitative analysis of phenolic compounds and antibacterial activity of fractions and aqueous, ethyl acetate, dichloromethane, acetone and methanol (50, 80 and 100% v/v) extracts of flowering herbs of C. acanthoides L. The antimicrobial activity of tested extracts was determined in vito against reference microorganisms of Gram-positive bacteria, Gram-negative bacteria and fungi belonging to yeasts. The results of this study support the medical usage of C. acanthoides L. due to its antimicrobial properties.


Asunto(s)
Antibacterianos/farmacología , Asteraceae/química , Hidroxibenzoatos/análisis , Extractos Vegetales/farmacología , Cromatografía Líquida de Alta Presión , Flores , Extractos Vegetales/análisis
19.
Saudi Pharm J ; 25(7): 1097-1102, 2017 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-29158722

RESUMEN

In this research we synthesized and tested for in vitro antimicrobial activity 21 nitrofurazone analogues. The compounds we obtained were identified on the basis of 1H NMR and 13C NMR spectroscopy. The in vitro screening of antimicrobial properties of synthesized compounds revealed a wide spectrum of antimicrobial activity. Compounds 28, 29, 32-43, and 45-48 showed very high bactericidal effect towards Staphylococcus spp. ATTC and Bacillus spp. ATTC (MIC = 0.002-7.81 µg/ml and MBC = 0.002-31.25 µg/ml). The levels of activity of several compounds were far better than those of nitrofurantoin, ciprofloxacin or cefuroxime.

20.
BMC Microbiol ; 16: 62, 2016 Apr 06.
Artículo en Inglés | MEDLINE | ID: mdl-27052615

RESUMEN

BACKGROUND: Haemophili are representative microbiota of the upper respiratory tract. The aim of this study was to assess the effects of perioperative antimicrobial prophylaxis and/or postoperative treatment on Haemophilus parainfluenzae prevalence, and antimicrobial sensitivity in short-term hospitalized patients with lung cancer who underwent surgery. RESULTS: Samples were collected from 30 short-term hospitalized patients with lung cancer and from 65 healthy people. The nasal and throat specimens were taken twice from each patient: before (EI, Examination I), on the fourth/fifth day (EII, Examination II) after surgery, and once from healthy people. The isolates identification and antimicrobial susceptibility were detected by routine diagnostic methods. H. parainfluenzae was found in throat specimens of 42/65 (64.6 %) healthy people, while in 19/30 (63.3 %) lung cancer patients in EI (p = 0.6203) and in 13/30 (43.3 %) ones in EII (p = 0.0106). Neither the disease itself nor short-term hospitalization with perioperative prophylaxis alone affected H. parainfluenzae prevalence in EII, while perioperative prophylaxis with postoperative treatment significantly decreased its colonization in EII. The differences in the number of patients colonized by Candida spp. in EI and in EII were observed (p = 0.0082).Totally, 23/58 (39.7 %) of H. parainfluenzae isolates were resistant mainly to beta-lactams; among 11 ampicillin-resistant isolates only 3 were beta-lactamase positive. CONCLUSIONS: The antimicrobial perioperative prophylaxis together with postoperative treatment may disturb the composition of the airways microbiota represented by H. parainfluenzae, in addition to selecting the resistant strains of bacteria and promoting yeasts colonization in lung cancer patients undergoing surgery.


Asunto(s)
Antibacterianos/uso terapéutico , Profilaxis Antibiótica/métodos , Infecciones por Haemophilus/epidemiología , Haemophilus parainfluenzae/efectos de los fármacos , Neoplasias Pulmonares/cirugía , Sistema Respiratorio/microbiología , Adulto , Anciano , Cefazolina/uso terapéutico , Cefuroxima/uso terapéutico , Farmacorresistencia Bacteriana , Femenino , Infecciones por Haemophilus/microbiología , Infecciones por Haemophilus/prevención & control , Haemophilus parainfluenzae/aislamiento & purificación , Humanos , Neoplasias Pulmonares/complicaciones , Masculino , Pruebas de Sensibilidad Microbiana , Persona de Mediana Edad , Nariz/microbiología , Atención Perioperativa/métodos , Faringe/microbiología , Prevalencia , Resultado del Tratamiento
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